Dimethyl Sulfoxide → HCID 22386456, Verbindung

HRID 2119320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2119320
[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[N:8][N:7]=1.CS(C)=[O:29]>CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[O:29])=[N:8][N:7]=1

Komponenten

5

Edukt 2

HCID 679Dimethyl SulfoxideHCID 6918616N-(3-bromo-4-methylphenyl)-4-(pyridin-4-ylmethyl)phthalazin-1-amine

Produkt 1

HCID 22386456HCID 22386456, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.22 g (3 mmol) 1-(3-brom-4-methyl-anilino)-4-(4-pyridyl-methyl)-phthalazine (expl. 14 h) and 336 mg (3 mmol) potassium-tert.butylate in 10 ml DMSO is stirred in an open vessel for 10 days at RT. Then the yellow mixture is diluted with EtOAc and water, the aqueous layer separated off and extracted twice with EtOAc. The organic phases are washed twice with water and brine, dried (Na2SO4) and partly concentrated. After adding 10 g of SiO2, the residue is dried in vacuo and the resulting powder put on top of a SiO2 -column. Eluation with dichloromethane/EtOAc (5:1→1:1→EtOAc) yields [4-(3-brom-4 -methyl-anilino)phthalazin-1-yl](pyridin-4-yl)ketone (A) followed by [4-(3-brom-4-methyl-anilino)phthalazin-1-yl](pyridin-4-yl)methanol (B). A: m.p. 249-250° C.; FAB MS (M+H)+=419/421. B: m.p. 240° C.; FAB MS (M+H)+=421/423.

Aufarbeitung

  1. customthe aqueous layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed twice with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationpartly concentrated
  6. additionAfter adding 10 g of SiO2
  7. customthe residue is dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-08f6603a8d714c798d9267e8807d66ad
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686347B2

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